Organic Letters
Letter
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(23) The spectroscopic data of diene 14 matched in all aspects with
literature data, see ref 6.
(24) Despite several trials of conditions attempted, in our hands the
RCM yields from 14 to 1 were no more than 20%. For the reported
procedure, see ref 6.
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(
14) Triene (S,S)-8 is readily prepared via a two-step coupling of the
corresponding C -symmetric 1,3-antidiene diol and allyl alcohol with
2
POCl3 (see refs 13a and 13b), or in one step by employing
phosphoramidite chemistry (see ref 12a). The C -symmetric 1,3-
2
antidiene diol can be prepared in two steps from bis(1,5-dichloro-2,4-
pentanedione)copper(II) complex (a) Matsui, K.; Motoi, M.; Nojiri,
T. Bull. Chem. Soc. Jpn. 1973, 46, 562−565. (b) Rychnovsky, S. D.;
Griesgraber, G.; Powers, J. P. Org. Synth. 2000, 77, 1−11.
(
c) Rychnovsky, S. D.; Griesgraber, G.; Zeller, S.; Skalitzky, D. J. J.
Org. Chem. 1991, 56, 5161−5169. We have routinely prepared the
starting copper(II) salt in >100 g batches and have found that, if it is
washed appropriately with diethyl ether, it can be stored for long-term
(
>2 years) at room temperature on the benchtop. The CM partner 9
can be generated from (S)-epichlorohydrin in two steps, see: Kubizna,
̌
P.; Span
355.
15) Venukadasula, P. K. M.; Chegondi, R.; Suryn, G. M.; Hanson, P.
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ik, I.; Kozísek, J.; Szolcsanyi, P. Tetrahedron 2010, 66, 2351−
2
(
(
Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791−799. (b) Garber, S.
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000, 122, 8168−8179. (c) Gessler, S.; Randl, S.; Blechert, S.
Tetrahedron Lett. 2000, 41, 9973−9976.
17) Switching from CH Cl (40 °C) to DCE (70 °C) is necessary in
(
2
2
order to reduce homodimerization of the CM partner 9 (type I olefin),
see ref 15.
D
Org. Lett. XXXX, XXX, XXX−XXX